HIT THE BUTTON (Part 1&2)
by Cindy Johnson
This story is about Cross-Dressing and a Loving Relationship. I’m still trying to become a better writer, so please be understanding with any of my errors or mistakes. (The Title will make sense in later chapters)
HIT THE BUTTON — by Cindy Johnson
Lisa and I have been together since pre-school. You see, our moms became friends since our first day at school, and we’ve been as close as twins since we met. Our moms became best friends, and Lisa and I had weekly play-dates at her house, which had a pool and was where the women liked to chat. Because we spent most of the time at her house, I learned to play her games, which included dolls, playing with her Barbie collection, and tea parties. I never gave it a second thought and enjoyed being her friend.
The two of us even looked similar, with the same blond hair and blue eyes. Even our height and weight were similar and were often mistaken for twins. We became inseparable, and throughout our school years, did everything together. There was never a fight or a time we can remember being upset with each other. It was uncanny how well we knew each other, and often completed each other’s sentences. Everyone always assumed we would be together forever, but of course life can throw a curve ball and change your world.
One weekend in our junior year of high school, Lisa came over excited when she told me they accepted her to go to Stamford on an academic scholarship. They accepted me at Ohio State for engineering after being turned down at Stamford. She was sad because she knew they did not accept me to her school and that it would be difficult for us to be apart, and tried to ease the pain.
“It will only be for a few years and we can see each other on holidays. We can Facetime every night and be there for each other. Besides, it will be good for you to make some new friends and meet some new people.”
After we cried and held each other, we both knew we would not be together and that it was time for us to grow up and spread our wings. My four years away went quickly, and I graduated with top honors and was offered a job in California as an engineer for a government contractor. Lisa applied to Law School and remained at Stamford after I started my job. We remained close but we both dated other people and actually had no intimacy since high school, which never included actual intercourse but lots of oral activity.
Life went on and I learned that Lisa was engaged to one of her classmates. I was happy for her and sad that my closest friend was going to be out of my life. After several years at my job, I became successful by coming up with some patents that made my company a great deal of money and recognition. Lisa was now an attorney at one of the large firms in LA, married to her college sweetheart going on 4 years. I dated and had lots of friends but nothing serious as I dedicated my time to work and my career.
One Year Later
It was mid-July, and I was celebrating my 25th birthday with some friends in San Diego one evening when I ran into Lisa, who was in town and heard about my celebration from my mom. It was the best birthday present I could wish for, and we spent a few hours after the party catching up.
She had just signed her divorce papers after catching her husband having an affair with one of her friends and was devastated. I consoled her and got her laughing about old times. It was like we were never apart. To make a long story short, we became a couple again after that night. She put in a transfer to work out of the San Diego office, and we moved in together three months later.
We picked up where we left off and we both knew at that moment that we were destined to be together. After a short time, we decided to get married and spend our lives as one. A month after our wedding, she asked me something that shocked me to my core, and revealed a secret that only my sister and mother knew about.
My sister came to town a few days before the wedding, and Lisa and some friends went to her bachelorette party a couple of days before our planned wedding. Apparently, after many drinks, my big mouth sister asked Lisa if I still liked to cross dress. She said it as she laughed and thought that Lisa would have known, since we had been so close.
“You really didn’t know? Oh my god, you two have been so close, I can’t believe he never told you. I feel bad now, don’t hold it against him. I’m sure it was just an adolescence thing.”
“Nope, I had no idea. He never told me about that, which is odd because we knew everything about each other. It’s probably my fault because I made him play all my girly games and with my dolls when we were little. We’re almost the same size so my clothes will probably fit him, I think it might be fun to dress him up sometime. I’ll let you know.”
The girls enjoyed the party; we married a few days later and enjoyed a week in Hawaii for our honeymoon. It was romantic, and we both knew we had found our soulmates and would be together forever. It was our destiny.
Our sex was great, not wild rodeo sex, but loving sex. As I wasn’t exactly large down there, I learned to please Lisa with my tongue and always brought her off with amazing orgasms. She always said she never came as hard as when my tongue made love to her sexy, smooth pussy. Lisa had the most beautiful pussy I had ever seen, and she kept it shaved and smooth, which I enjoyed when I pleased her with my mouth. When she was excited and about to come, her clit would enlarge and pop out of her tight pussy lips, and I knew exactly how to suck and tease it until she was screaming and pushed me away.
A month after we were back from our honeymoon, she brought up the cross-dressing question after another great night of sex. We were cuddled together after another wonderful love making session when she asked me about it.
“Jason, why didn’t you tell me you used to dress up like a girl when you were younger? I thought I knew all of your secrets, so you can understand why I was surprised when Sally asked me if you were still cross-dressing.”
My entire body tensed up, and I felt my stomach do a flip as I realized that my big mouth sister told Lisa my deepest secret, which only she and my mom knew about. I tried to act cool and nonchalant but it was obvious she reached deep into my soul with that question.
“Well, it was so long ago I didn’t think it was important. I was embarrassed when mom caught me and didn’t think it was something I wanted to share with anyone. I’m sorry I didn’t bring it up, but since it was so long ago, I didn’t think it was important.”
“You’re right, it’s not important. I was just surprised I didn’t know about that part of you. I mean, we’ve always been so close I really thought we knew everything about each other. Is there anything else I didn’t know about?”
“No baby, that’s my darkest secret. I always tell you everything and I know you do the same, which is the most important thing in our relationship. Our total honesty and openness are something I’ve never had with anyone else except you, and I love that we trust each other completely. I’d never lie to you, and I know you would never lie to me.”
We kissed and hugged and eventually fell asleep after several minutes in each other’s arms. Life continued, and our marriage was perfect. We spent every minute together, making sure the other person was happy and satisfied. We were again as close as any couple would be and we loved each other unconditionally.
One Saturday after Lisa came home from the cleaners, she was putting her dresses away and came out of the closet with a dress in a plastic bag. She held it up to my body as I stood there wondering what she was doing.
“Sweetheart, I just saw this old dress in my closet, which I never wear anymore, and thought that it probably would fit you. Would you let me play dress up with you today? You remember how we always played dress up with my dolls, well today I’d like you to be my real-life doll, and let me dress you up. What do you say, would you let me do that?”
I felt my face turn red from embarrassment at her request, but at the same time, I felt my excitement stir at her question. Trying to remain calm and not give myself away, I told her I’d be happy to be her doll for the day and it would be like old times.
“Goody, I can’t believe you’ll let me do this, I love you so much! It will be so much fun, and I promise you’ll make you very happy in bed tonight, as a repayment for being so kind and letting me do this.”
“I like the sound of that, and I’ll take you up on your repayment in bed tonight. I hope you’re ready for a fun night.”
“You will be smiling all night, baby, I promise. Now, I want you in the shower and I want your legs shaved and smooth. Use my lotions and razor and then come back in the bedroom and I’ll get things ready.”
I probably should have protested and acted like I didn’t want to, but the truth was that I did want to play dress up with her. In fact, it had been a fantasy I kept hidden, and never in a million years thought I would ever have this opportunity. With this in mind, I was going to do whatever she wanted and just enjoy everything about it. The best part is that it was her idea, which left me guilt free. After all, I was doing this for her.
True to her word, there were piles of lingerie on the bed and several pairs of shoes next to the makeup table. She had a big smile on her face, and was clearly going to have fun with me as her real-life Barbie Doll for the day. She had me stand in front of the bed and picked up several pairs of panties and bras until she selected the matching set she wanted me to wear.
She was happily surprised with my familiarity with the garments, and commented on how nicely I put on the pantyhose without getting a run in them. She placed some padding in the bra, adjusted my pantyhose, and then took a step back to admire her work.
“That looks perfect, and it looks like most of my things will fit you. You’re only a couple of inches taller but we have similar body shapes, except for your bust, which we can easily fix. Oh, this is so much fun. I can’t believe you never told me about this, we could have played dress-up all those years when we were younger!”
She sat me at her makeup table and expertly used all of her products to create a perfectly feminine outcome to my face. She smiled as kissed me when she was done and then started working on my shoulder length hair, using clips and hairspray. The image in the mirror made me smile when I realized I could pass for her sister. With the same color hair and eyes, and being similar height, we could actually pass as twins with a little more effort.
“Oh my goodness, you’re beautiful. I mean, you really are pretty, and this is just the first time we’ve tried this. You have to promise me we will do this again, I just love dressing you up like this. What do you think, how do you think you look?” she said as we stood next to each other in the full-length mirror.
“To be honest, I can’t believe I look this good. I mean, you really did a number on me, and if we wore the same outfits we could pass as twins. I definitely will let you do this again, as long as you’re OK with your husband looking like your sister,” I said with a grin.
She laughed, “Oh honey, I don’t care about that. You’re my soulmate, and I love everything about you. We are one, and I could never think badly of you. I’ll love you forever, no matter if you’re in a dress or my macho hubby. Right now, I like you in a dress, and it’s making me wet. I need your tongue inside my pussy, right now, baby.”
For the next hour I brought her to three screaming orgasms with my mouth and another one when I came inside her to finish the evening. We collapsed, and I fell asleep still dressed in her lingerie and makeup. It was one of the most exciting sexual times we’ve ever had together, and she commented, ‘we will need to do this more often.’
All of the dressing brought back so many memories. They were memories that I had suppressed but were now coming to life. Wearing that cute dress with the lingerie and high heels felt electric and exciting. And being able to share this with Lisa was indescribable. It was a dream come true, and I knew we would do this more often.
We repeated the same game every Saturday until Jason returned Sunday morning. There were now seven outfits that Lisa didn’t wear that became part of Amanda’s wardrobe. Amanda became my name when dressed, which was always a one of Lisa’s favorite girls’ names.
She made space for a section of her walk-in closet for Amanda, and soon I had a nice selection of clothes to wear each week.
Lisa’s sister was a makeup artist in LA and over the years had taught Lisa some of her makeup skills. After several dress up sessions, Lisa started teaching me the same skills, and after a few weeks we were putting on our makeup in front of the mirror side by side. Two girlfriends getting dressed for a day of shopping, dining, and dancing. Yes, dancing. Living in California is a cross-dresser’s dream. Others always accept us, and going to dance clubs is a normal part of life for our age group, and we enjoyed ourselves. There were several clubs we went to after our Saturday night dinner, and enjoyed the evenings together as girlfriends.
We often danced together and enjoyed listening to the music with a glass of wine. Guys were constantly asking Lisa and I to dance, and we both agreed to limit ourselves to 2 dances per night with any guys that hit on us, in order to be cordial, and to enjoy the experience as girlfriends without having to worry about each other. We never danced unless the other was dancing at the same time, and we always kept an eye out for each other. I even admitted to Lisa that dancing in a dress and heels was fun and that I liked it. After a few weeks and several dances with men, I became comfortable enough to just enjoy the feelings and being Amanda. Other than a hand on our ass or a quick kiss, nothing happened, and we always shared notes back at our table after we told the boys we weren’t looking for company.
Giggling and laughing at our exploits was something I had never anticipated but enjoyed. We would tell each other how the boys tried to flirt or touch us and if we made them hard, or how big they were. In fact, we both enjoyed our nights out as girlfriends more than I ever dreamed, and were now closer than ever before.
As I mentioned, the area of the country we lived in was accepting of our lifestyle and we had no issues when we went out together. However, the lack of feminine movements gave away my gender, which continued to inhibit my openness and willingness to try new things. Even though my appearance was clearly female, my hand movements and the way I walked gave away the fact that I was not a true female. Every Saturday we would get Amanda dressed up, and we went out to trans friendly places, had dinner and went to movies, and even some festivals on the beach.
Over the many weeks, Lisa continued to coach me on my movements and wanted her Barbie Doll to become her real-life girlfriend. I was an eager student and learned many of the feminine secrets she grew up with, and practiced them every Saturday afternoon until we went out that night.
Our Saturdays became a ritual play date and started as soon as we got out of bed that morning.
Lisa had made friends with Mark, one of the senior partners at work, who had a boyfriend that we met and went out with. Several Saturdays, we ended up double dating with the boys. We were two girls out with the two guys, and nobody gave us a second look. It was an interesting dynamic, which made me comfortable as Amanda, while out with men.
Since there was no threat, we even split up and danced together. Mark would dance with Lisa, and I would dance with Steve. In fact, we did this so often that I became comfortable dancing as a girl, being held, and following during slow dances, and falling into the female role. Several times Lisa commented about how proud she was of my progress, and how natural I was becoming in my movements and confidence.
Lisa and I were out alone one night when two of the local military servicemen came to our table and asked us to dance. It turned out that the man interested in Lisa was Dawson Dakota, the commander at the naval base and a well-known ladies’ man. He was a big guy, and Lisa looked tiny while she danced in his arms. I danced with Joey, one of his friends, but I was clearly not his type. But he kept me company, as he was Dawson’s wing man. We sat together, and they bought us drinks all night, and for the first time, I saw Lisa enjoying herself with another man other than me. It was obvious that she was infatuated with this big tough guy and his status as a Naval officer. She was giddy and flirting like a schoolgirl, which made me a little uneasy and jealous.
Seeing her with another man confused me, and brought up new emotions I couldn’t explain. That night in bed while in each other’s arms, I asked her about Dawson and how she acted.
“That was a fun night, and you really seemed to enjoy being with Dawson. It kind of made me jealous to see you flirt with him like that,” I said with a shaky voice.
“Oh, sweetheart, I love you. Don’t be jealous, I was just having fun, and you were right there the entire time. It was just different with him, I mean, he was so big and strong and he made me feel, well, different. I love you and don’t want anyone else, but it’s hard to explain, I just had fun. I love you and would never want anyone else, honey,” she said as she kissed me gently and stroked me to another orgasm. She cleaned me up, and we fell asleep in each other’s arms.
The following days I noticed she was answering more text than usual and asked her about it.
“Who have you been texting to, baby?”
“Just Dawson, he’s been telling me about his upcoming hiking trip.”
“How did he get your cell number?”
She saw the sad look on my face and quickly reassured me, “I guess I gave it to him at the club. I’m sorry. Should I not have given it to him? I can stop if it bothers you honey, he’s just a friend.”
Not wanting to appear jealous, I just smiled and said, “It’s OK to have a friend, but remember, I’m your husband. I can’t compete with a guy like that, and I hope I’m not losing you, honey. You know I can’t live without you.”
“Never, baby. It was fun being out with Amanda and kind of being on a double date with Dawson and his friend. I mean, you seemed to enjoy dancing with him and spending time that way. It’s just fun, let’s not make it anything else, baby. Besides, he knows I’m happily married, that I love you, and that I’m dedicated to our marriage.”
The texts continued, and they became good friends, but Lisa was great at keeping him out of our relationship. I knew nothing was going on, and she was happier than ever, so I just observed and allowed life to continue.
My Job had an upcoming closure. Every year we closed for a month in coordination with our government contracts. I would usually spend the time lying around or going to the beach. This year, however, Lisa had an idea that eventually changed things forever.
A week before my time off, we were out on Saturday night. Lisa had made reservations at the C-Level Lounge on the harbor. We wore the new outfits we purchased the previous week, along with our sexiest lingerie and high heels. She wanted us to look extra cute and have a dress-up date night, and by that time, I was happy to go along with her plans. She had me dressed in a pink silky sheath dress that fell to mid-thigh. I wore a pair of thongs under my suntan pantyhose while it tucked away my small penis, which remained unseen under the flowing skirt.
Lisa wore a black silk dress that also fell to mid-thigh, but under that, she wore stockings attached to black lace garters. I loved how the top of her stockings peaked out when she crossed her shapely legs. I also loved the attention we both received by the other guest. Having two sexy dressed girls eating alone attracted a lot of views from the other patrons.
While we were on our second glass of wine, Lisa made an amazing request, which I didn’t know how to answer. She smiled and went on about our life together.
“Amanda, this is so much fun, and you’ve become perfectly feminine. Your hand movements, the way you cross your legs, and your voice is just perfect. Not one person could read you as a man. We’ve made substantial progress over the last six months. But I have a suggestion to get you over the top and really establish your female side if you are willing to go along with it.”
“Thanks Lisa, I have to admit I enjoyed becoming your girlfriend on Saturdays. To be honest, every Wednesday afternoon I find myself looking forward to the weekend and becoming Amanda with you, so what did you have in mind?”
“Well, I thought that maybe you can become Amanda for longer than one day. I was thinking that maybe we could immerse you as Amanda for your entire shut down, four weeks of living as Amanda, twenty-four hours a day. Just think about it, you can get your nails done, your hair is cute now, but we can get some extensions and really spice things up. You’ll have a chance to see what it’s like to live as a woman for an extended time and learn things that would take years to acquire. I’ll be your girlfriend and totally supportive, protect you, and teach you everything I know. What do you think?”
“Wow, I don’t know what to think. I mean, I really enjoy doing this with you, but full time for a month? How would that make you feel without having me around as your husband for that amount of time?”
“I think it would be fantastic, and my hubby would be my girlfriend. I love how sexy she is in my bed, and I really enjoy how she gets me off. I think it would be a fun experiment, and a learning experience for you, baby. Let me know soon because we will have to get lots of new clothes to last the month. Think about how much fun we will have shopping and buying you all new lingerie and heels. I can’t wait, I hope you say yes.”
We finished dinner and drove over to Rich’s dance club. This club is big and friendly to all types of people with two dance floors, and lots of room to have fun. Her friends Mark from work and his boyfriend Steve were already there and had a table for us near the dance floor. We ordered several bottles of wine, danced, sang, drank, and had a great time all evening.
While we were drinking, Mark extolled his compliments on how I’ve progressed in my feminine appearance. “You girls make such a cute couple and I have to tell you, Amanda, you really have become quite the young lady. The way you speak and movements have become one hundred percent female, and if I didn’t know you were Lisa’s husband, I would swear you were really a naturally born woman, and Lisa’s girlfriend. I’m amazed, and I know you can tell how pretty you have become by the way all the guys look at you and ask you to dance. You really are quite lovely and I’m happy for the both of you. You two make the perfect couple.”
Lisa and I beamed with a smile at his compliment. Lisa was proud of her work, and I was excited to hear that I had progressed to the point of being considered a passable female. Lisa and I already knew we were the perfect couple, and kissed each other after his compliment. I looked at Lisa and told her how much I loved her and how happy I was to have her as my soulmate.
At the end of the evening, Lisa and I were lip locked on the dance floor. As we explored each other’s body, Mark and Steve smiled as they watched the action. At this club, and at this time of night, two girls’ kissing was considered normal, as others were grinding and sexing at the same time to the music.
We took a cab home and when we got into bed; we made crazy love for the rest of the evening. Sharing our lipstick covered lips in kisses was exhilarating. Rubbing her stocking tops and feeling Lisa rub my cock under the pantyhose was outrageously sexy. We both came several times until we collapsed into the wet spots on the bed and slept until noon the next day in each other’s arms. It was one of our hottest nights ever and we both know we wanted more of the same.
The next morning, I gave her my answer and said, “If you were serious last night, I decided to take you up on your idea and become Amanda for my entire time off.
Do you still want me to do that?”
“Oh, God Yes! I love it. Thank you, baby, you won’t be sorry. I promise you it will be a blast and you’ll love every minute.”
Part 2 of 5
Four wonderful weeks as Amanda
The shutdown was approaching, and Lisa was helping me prepare to live as Amanda for the next four weeks. We spent several nights at the malls and boutiques shopping for cute outfits and dresses. Since she was one size smaller, she tried on the outfits when we were out and knew what would fit me. Since we were about the same size and shape, what looked good on her would look good on me. Shoe shopping was the same. She was a size 7 shoe, and I was a size 8, so when she tried on shoes and we found the ones she liked, she had the salesperson go back and get them in my size, which confused him but did what he asked.
Since I could use her cosmetics, we had no need for more, but we got my ears pierced the Saturday before my time off. She also surprised me with a salon appointment with her stylist the same afternoon. By the end of the day, I had hair extensions with wonderful curls that fell to the middle of my back. Long, thick blonde hair that matched perfectly with my own. By the time we got home that night we just jumped in bed and made love all night, from the exciting day of shopping and knowing that Amanda would be her girlfriend for the next month.
The next day we had breakfast, and I was struggling with my long hair, which was constantly getting in the way. Lisa just giggled and said, “You will have to get used to having long hair now, and soon it will feel natural to flip your hair, which will even make you look more feminine, if that’s even possible. Your hair really looks good on you and with all those curls, there is no way anyone would think of you as a man. This is going to be fun; I hope you’re as excited as I am, baby.”
“There is something I was thinking about and want you to consider. Once Amanda comes to stay, I think it would be wise if she thought like a female at all times. If we’re going to immerse her in being a girl, she can’t go back and forth between male and female. What I’m saying is that I want you, Amada, to have only feminine thoughts at all times. If you have any boy thoughts, you need to catch yourself and start acting and thinking about girly things.”
“I’ll coach you, but you’ll need to talk, move, act, and think like Amanda, every minute during this month in order to become her, and understand the female side of life. This was my goal for you all along, and I want to help you really enjoy and understand what being a woman is all about. Does that make sense?”
I tried to understand and consider her logic. It made sense, but I wanted to make sure she was going to be OK if she was living with a girlfriend instead of a husband for a month.
“Lisa, I can do that and it makes sense, but are you sure you’ll be OK with that. I mean, will you forget about me as your husband? I can’t lose you, and I won’t do this if it jeopardizes us.”
“Sweetheart, this is what I want, and as long as you’re with me, I’ll be happy. You’re all I need, whether you’re Amanda or Jason. Do you understand, it’s you I love. Not the clothes or anything else. My love for you is so much deeper, and I will love you forever.” She kissed me tenderly and relieved my fears. I said I would try to stop any male thoughts and live the full month as Amanda, and become her in every way she wanted.
Monday morning was my official first day as Amanda. Besides dressing all day as a female, I had to improve my makeup skills and keep myself in a feminine mindset at all times. Before she left for work, Lisa gave me some chores to do for that morning and instructions for my afternoon. For the next month, I agreed to be in charge of all the household duties, including laundry, ironing, changing the sheets, vacuuming, food shopping, cooking dinner, and keeping the house clean.
After the first few days, I was able to get into a routine and have everything complete before she came home at 4pm. I dressed nicely, with perfect hair and makeup, which she inspected when she got home.
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On the second night of this adventure, Lisa came home with a bottle of pills and explained, “Amanda, you know that Steve, Brian’s partner, is a doctor and an endocrinologist. I explained to Brian what you agreed to do for the month, and he told Steve last night. Today Steve called and said that these pills will help you focus on keeping any male thoughts away during this month. He sent a prescription over to CVS, and I picked it up for you on the way home. Isn’t that great, you will be able to really focus on Amanda without your nasty testosterone getting in the way.”
“Exactly what are these pills, Lisa?”
“Steve prescribed a new drug. It’s a combination Testosterone Blocker and Female Hormones that will stop your testosterone development as long as you’re taking them. He said this new drug combination will have immediate effects, and will become noticeable in about 7–10 days. And the good news is there won’t be any long-term side effects, since you’ll only use them for a month. Go ahead, take your first pill,” she said, handing me the bottle.
I hesitantly considered her idea, but she looked so excited that I took one and placed the bottle on the counter. She came over and hugged me, and gave me a sweet kiss on the lips. “I love you so much baby, you’re so perfect in every way,” she exclaimed with lots of enthusiasm. She seemed to be more excited about this adventure then I was, which is saying a lot, because I was having lots of fun living as a female.
We continued to have great sex and enjoyed our lovemaking. At first it was strange to make love to Lisa as Amanda, but our excitement overcame any of my concerns. My biggest problem was my very long hair getting in the way while we made love, and just trying to sleep. I was now constantly moving the long hair away from my eyes. Lisa always commented that I looked very feminine and naturally doing that, as every girl with long hair was used to. She taught me how to put my hair up in a bun or tie it back with clips, which helped me throughout the day.
Trying to keep myself immersed in my female persona, I tried to spend any free time watching makeup videos, reading fashion magazines, shopping for new outfits on-line, and reading romance novels that Lisa purchased for me. She brought home many feminine magazines and books to read in order to keep me focused. We even sat together in bed discussing some articles regarding men, dating, fashion and taking some type of quiz to see what type of man you’re compatible with.
At first I objected to any conversations regarding men, but Lisa pointed out that every girl has these conversations and it forms their personality and thought processes. She wanted me to experience these things and help understand the female thought process. There were times she pointed out men in the magazines and would ask me if I thought he was cute, and If I said yes, I had to explain what I liked about him. It was awkward at first, but after a while I understood what she expected, and got into the role playing she was encouraging.
A week later, I noticed I was no longer getting erections, and my penis seemed even smaller than usual. I pointed that out to Lisa, and she said that was one effect of the pills, and not to worry because it will work again when we stop. She wasn’t upset that I couldn’t penetrate her during sex, because she still enjoyed my oral skills, which always satisfied her. I realized that I didn’t have a strong need to ejaculate and was just happy to hold and cuddle in bed after satisfying her needs.
The second week, I found the routine was becoming normal. Lisa had created a practice program for my feminine movements, and every day I spent two hours working on these skills. She had me practice walking, sitting correctly, crossing and uncrossing my legs, walking in heels, and paying special attention to my arm and hand movements.
After spending one afternoon getting long acrylic nails, I found that my hand movements became even more feminine and graceful because of the length of my nails. They looked spectacular, but were tricky and difficult to master. Lisa taught me how to use the pad of my fingers and how I needed to move my hand more carefully and gracefully. The result was that by the end of the second week; I was as graceful with my movements as any woman we knew.
The primary effect, after breaking two nails and having to go back to the nail salon to get them repaired, was that my hand movements became much slower and feminine. Between my long hair and nails, my hand moments were now naturally feminine, and combined with my practicing in heels for two hours a day, I was now comfortable and confident as Amanda.
By the second week, I was food shopping and spending some time alone at the park. Several times I sat by the lake and gave thanks and gratitude to the world for my life and Lisa. I realized I had the most amazing wife and partner in my life. I was living out a long-time fantasy, and spending extended time as Amanda. Our financial situation was exceptional, and we were both healthy and enjoying our wonderful lives together as loving couples.
On Wednesday night, Lisa sat and observed how I served dinner, how I handled my dining, and even how I held my wine glass. My hair and makeup had become expert, and I always looked perfect for her when she came home. My voice was easily passable and the overall look was of an attractive girl. Our conversations also impressed Lisa, which showed no male interaction. We gossiped about people at her work, some new shoes I saw on a girl that day, what movie we should watch, where we should go dancing that weekend, makeup or hairstyles, and feelings. Lots of conversations about feelings. Getting in touch with my feelings and talking about them was new to me, and one of the hardest things I had to learn. I had to discuss how I felt about my looks, my desires, my life, and just about everything Lisa could come up with until I was comfortable to discuss each topic from a female perspective.
Lisa was pleased with my results and my overall development in less than two weeks. The speed of my transition to Amanda made her happy, and she wanted to celebrate that Friday evening. She said that she wanted to spend more time with Amanda and took some time off to take advantage of having her girlfriend around until next year’s break. She invited Brian and Steve to join us and celebrate my development and have a fun evening together. We planned to meet them after dinner at one of the local clubs.
That Friday night, Lisa and I went out to dinner and the Seaside Overlook. We dressed up for the evening in our little black dresses, stockings, and high heels. Our make-up and hair looked perfect for evening wear. Our long blond hair and blue eyes, against the black dress, made us look a little sexy and desirable. We outdid ourselves and wanted to have a fun night out on the town. We planned to make this a special night together as we enjoyed our time together.
During dinner, I told Lisa how happy she made me and that I was enjoying my time as Amanda. I explained at first I didn’t think it was a good idea, but now I was glad she convinced me to live this way for the four weeks.
“Lisa, I always loved the idea of dressing up and acting feminine, but I had no idea it would be such a soul touching experience. And being able to enjoy this part of me with you was the best thing I’ve ever done. Thank you for pushing me to do this. I know I balked at your idea, but I’ve never been happier.”
Lisa had the biggest smile on her face, and beamed with pride in giving me something with her I had never had, the chance to live out my deep secret. We always wanted the best for each other, no matter what that was, and being able to give some happiness to the other person was the most satisfying feeling we experienced as partners.
While we sat at the restaurant with big grins on our faces and enjoying our time together as girlfriends, Tom Williams, my boss from work and his wife, walked past our table and then stopped suddenly, turned around and came back to where we were sitting.
“Lisa, is that you?”
“Yes, it is. Hello Mr. Williams.”
“Please, not so formal, Tom is my first name. This is my wife, Veronica. Veronica, this is Lisa, the wife of one of my best engineers.”
“Nice to meet you, Lisa.”
“Nice to meet you as well. This is my friend Amanda,” she said as I sat there nervously.
Tom reached out to shake my hand to say hello. I carefully gave him my hand as a woman would, and he took it gently into his own large hand. At that moment I saw him look down at my dainty hand with my long pink nails, and then I saw his smile turn to confusion as he noticed the birthmark on my wrist.
I was born with an odd shaped birthmark on my wrist that had the shape of the Nike Swoosh. It wasn’t very noticeable, but Tom and I joked about it over lunch several times, and for some reason, it became an inside joke between us.
Tom is a highly intuitive man, and when he saw the birthmark, I saw his eyes open wide and look at Lisa. That’s when he put two and two together. He looked back at me, and with a shocked expression, made the connection.
“Jason, is that really you? Oh my god, you’re beautiful. What’s going on?”
Lisa noticed other people looking in their direction and said, “Please Tom, sit with us for a few minutes and we can explain.” Tom and Veronica took a seat at our table as Lisa took over as I sat there afraid to move or speak.
“Tom, this has to remain our little secret. My husband enjoys to cross-dress and we are out role playing. In fact, I convinced him to live as Amanda during your shut down. This was all my idea, and I coerced him to dress this way, so please don’t think poorly of us.”
They smiled and looked at Veronica, who spoke up, “Well, all I can say is I’m happy for the two of you. Amanda is a beautiful woman, and you’re both lucky to share your desires. I would love to spend some time with the two of you, maybe we can all do some shopping together?”
Lisa smiled and said, “That would be fun, wouldn’t it, Amanda? You’ll have a new friend that we can go out with.” I just smiled and nodded as I sat there in total fear.
Tom spoke casually, trying to put everyone at ease, “Amanda, what’s your plan after we get back to work? Are you going to come back as Amanda?”
Frozen in fear, I watched as I saw Lisa’s face light up as she asked, “Tom, is that an option? I mean, would that be possible for her to come back as Amanda?”
“Of course. We’re a government contractor and follow their guidelines and we welcome all lifestyles. I know the team would have no issues with that, and coming back as Amanda would probably help my gender compliance with the HR team. In fact, it might actually be a benefit. But yes, if you came back as Amanda, we would be happy to accommodate the transition. Call me and let me know,” he said, handing Lisa his business card. After a few minutes they stood up, smiled, and left us alone as they went to their table with their guest.
“God, Lisa, I thought I was going to have a heart attack. That was so uncomfortable.”
“Nonsense, that was amazing. I think it went well and if your birthmark hadn’t given you away, nobody would have had any idea. I’m just so proud of you, baby. He seemed honestly accepting of you as Amanda.”
“I’m sure you’re right, but that’s the first person I’ve met that now knows about me.”
We finished dinner and met Brian and Steve at the club. As usual, they had a nice table next to the dance floor and a bottle of champagne waiting for our arrival. Lisa told the boys that were celebrating my successful transition into the female world.
They stood up and welcomed us with a hug and a gentle kiss. “Wow, you girls look hot. The way you’re dressed will drive all the men wild tonight, and with no satisfaction. The two of you are such a tease, you’re lucky you have us here to protect you. But seriously, you both look amazing in those dresses, if we weren’t gay, we would take you to bed, right now.
We all laughed and drank the champagne after Lisa made the following toast.
“To my beautiful Amanda, we are all proud of you and I’m the luckiest girl in the world to have you as both my husband and girlfriend. Thank you for being you, and putting up with my wild ideas.”
It was a fun night as we finished several bottles of wine, danced with several good-looking guys, and I even got to practice some flirting. Lisa pressured me when we were in the girls room earlier that night. She wanted me to try some of the flirting moves we practiced as a new experience. It was fun, and I enjoyed the power I seemed to have over big, powerful men. It was an eye-opening experience, but of course nothing was going to happen, because there was only Lisa and me in our universe.
Sometime much later that night, a taxi dropped us off at our front door. We rushed inside, visited the bathroom and met each other in bed where we ravished each other’s lips and wonderful bodies. Any memory of our conversation with Tom earlier that night was forgotten.
Lisa went to see Tom the following week and confirmed that, in fact, Jason could come back to work as Amanda. She wanted to make sure that Tom was serious, and everyone would be OK with the change before she talked to Amanda about it later that night.
She knew their love for each other was genuine, and knowing that her husband was excited and happy about living as Amanda made her smile. She loved making him happy, and Jason presenting as a female made no difference to her feelings. In fact, Lisa now felt closer to her husband than she had in all the years they’ve known each other.
She was going to suggest that Amanda stay around for at least another month, and go back to work as the girl she has become. She loved him deeply and just wanted him to enjoy this as long as possible. Lisa knew he could always give up living as Amanda, but they’ve come so far, it would be a shame to stop now, given the opportunity to go back to work as a woman.
When Lisa got home on Monday, Amanda was folding some laundry and looking so cute in her floral sun dress, high heels, and full makeup. It was becoming a normal scene, and neither of them blinked or felt odd about their living arrangement. Lisa took Amanda by the hand and led her over to the couch. They sat and held hands as she spoke.
“Honey, we need to talk,” she said.
“Sure honey, what’s up?”
Lisa smiled as she saw how Amanda was sitting at the edge of the couch with her legs crossed and her manicured hands on her lap. So naturally feminine, she thought to herself.
“Sweetheart, I called Tom, and we met for lunch to discuss you going back to work as a female.”
Amanda looked shocked and waited for Lisa to continue.
“I wanted to see if he was serious about your coming back to work as Amanda, and how the staff would react. He assured me he was serious and said the staff would have no problems, as they are all open to different lifestyles.”
“Wow, you talked to my boss? And he said it really would be OK to come back as Amanda?”
“Yes, how do you feel about that, baby? I see how happy you’ve been since we started dressing this way, and I think it would be something you would like to do. Since I love having Amanda around, I would be OK with it, I think you should do it.”
“That’s crazy. Are you telling me you would be OK if I stayed this way? I mean, as you husband, doesn’t it bother you that I would live with you as a woman and not a man?”
“Sweetie, don’t be silly, you know how much we love each other, and what type of clothes you wear makes no difference to how I feel. We’re soulmates, and have been that way since we met as children. Most of the times we finish each other’s sentences, and know what each other is thinking. I can’t live without you, and seeing how you are this way only makes me want you to continue until you want to stop. I love you either way, but this is an opportunity for you to live as the girl you’ve always wanted to be, so I say yes, do it.”
I was worried about how this change would affect our relationship. The pills I’d been taking were now preventing any full erection, and I barely got hard enough to penetrate Lisa, but apparently our oral engagements were enough for her, as she never complained and only encouraged my female role as her girlfriend.
Lisa never stopped moving this forward and announced that she spoke with Doctor Steve, and could get the drugs renewed for 90 days. I had to agree to go to his office for some blood work as a precaution, as the drug was new and had just received FDA approval. I could tell the pills were working, as I was much more submissive and relaxed with heightened emotions. There was an increased tenderness in my nipples, and my breast had become puffy, just after a few weeks of use. This new drug definitely was making some changes which kept me soft and compliant, and happy.
The next day Lisa came home from work smiling and told me about her day as she handed me my prescription refill.
“I picked up your pills today, baby. You know my friend Karen, that I always talk about, right? The girl that is hooked on Botox and plastic surgery, remember?”
“Yes, the pretty girl with the amazing long blond hair?”
“Yep, same one. She just got her lips done and they look amazing. You know I think you’re really pretty, and everyone that has seen you think you’re a CIS female, but there is one thing that I think you can do to really enhance your looks, and put you over the top, and that is to have your lips done. Right now, they are a little thin, and some enhancements will really add to your feminine appearance.
I spoke with Karen and she gets a good deal from all the work she had done, and we could get you an appointment for tomorrow afternoon. She got us a 50% discount, and I want to pay for it as my gift to you. What do you think, honey?”
“Wow, I don’t know what to say. Fake lips, is that the right thing for me to do?”
“That’s Hilarious. You already have fake boobies, hair extensions, and pierced ears, what would be the difference, except those lips would make you look like a supermodel and very appealing. I’m all for it, and I might even get mine done as well. It’s settled, and we are going there together when I get home tomorrow.”
True to her word, the next night I had several syringes of something injected into my lips, and I was stunned at the results. I now had what men would call Cock Sucker lips, but the doctor explained that in a few days the swelling would go down and they would look much more natural.
The last week before I had to go back to work was hard for me, as I realized I would come out to the world as Amanda, as I worked and lived full time as a female, and married to my wonderful wife Lisa.
With mixed emotions, the week was going by too fast, and Lisa kept me busy. While she was at work, she had me go out alone to the Nail Spa, the Waxing Salon, and the dress shop for some final fittings on the new work outfits we purchased.
On Saturday, I had a full afternoon scheduled at the hair salon, where they were going to work on my extensions and touch-ups as needed. When I left there, Lisa wanted me to look perfect in order to give me the confidence to walk into work as Amanda for the first time.
We celebrated Saturday night and had to fight off several guys that continued to hit on us all evening. We finally danced with a few of the better looking guys, then went home and ravished each other’s bodies for the next two hours. Lisa loved the feeling of my lipstick lips on her pussy, and she always came in minutes after we got started. After several orgasms, we were able to get my small member hard enough to stroke it to a wonderful release. There was almost no fluid, but I felt as if I had shot a gallon of cum from our lovemaking that night. We slept in each other’s arms, kissing and cuddling all night long.
Amanda Goes Back to Work
Lisa drove me to my office on Monday, my first day back at work, but now as Amanda. I sat in the passenger seat looking down at my manicured nails resting on my lap, and touching my nylon covered legs, and smiled. The feelings were overwhelming, and I was happy and excited about my new life at work.
After giving Lisa a kiss, I opened the car door in front of the office building. There was a wave of fear that overcame me, and I sat frozen in my seat. I realized I would be completely on my own, returning to my work environment where everyone knew me as Jason a little over a month ago.
Lisa touched my shoulder and said, “Sweetheart, you look wonderful, and you’ll do great today. Take some deep breaths and relax, you’ll do fine, trust me. Be sure to call or text me with updates today, please. I love you.”
After forcing myself out of the car, I made it up to the seventh floor with no issues or odd looks and walked to my Tom’s office, and knocked on his open door.
“Hi Tom, I’m back. Are you sure this is going to be OK?” I asked nervously.
Tom looked up and gave me a warm smile before he stood to welcome me. “Good morning, Amanda, welcome back. Don’t give it another thought, you look absolutely stunning, and I have notified the staff about your change and they are excited about working with you. Now, I have some new files for you to work on, and I’ve sent them over in your email this morning. Let me know if you need anything.”
Tom went back to the paperwork on his desk, dismissing me and treating me just like he did before. So far, things seemed to go well, and I relaxed just a little and headed back to my desk. The professional and easy way Tom spoke with me allowed me to relax, just a little, as I realized that this might just work out.
When I got there, it shocked me to see a floral bouquet and a note from the staff that read, ‘Welcome Amanda, we’re happy you’re on our team. We’re here if you need anything, signed — The Team.’ The Team composed of 16 people that worked together for Tom. We have been a tight-knit group, and coming back to them as Amanda was my biggest worry, but it appears as if they’ve accepted me as a woman. I smiled and felt a tear in my eye. Lately I found myself more emotional and crying more often, which I know resulted from the pills I’ve been taking.
The day went by quickly and it was already lunchtime when two of the girls told me to join them for lunch. We drove over to “Salad Heaven” and ordered. Mary and Kelly were so sweet and have been super supportive and extra nice.
“Amanda, we are so happy for you, and you look amazing. Your hair is beautiful, did you get extensions? Tell us the name of your stylist, they’ve done wonders on you. You’re going to give us lots of competition around here if you keep dressing and looking this cute.” We all laughed and chatted about work and what we did over our break.
Oddly enough, they did not quiz me on why I was dressing this way, or anything personal. They just treated me as if I’d always been Amanda, and by the end of the day, I felt safe and welcome.
Lisa was so happy to hear how my first day went and couldn’t stop smiling. She gave me a warm kiss and said, “I’m so happy for you, baby. Was being Amanda on your own as good as you had hoped? I know you were nervous when I dropped you off, but I knew you were ready and looked amazing today. Tom called me and reassured me that everyone was excited and accepted Amanda with no problems.”
“When you dropped me off this morning, and I walked in by myself dressed in a skirt and heels, I thought I was going to have a heart attack, but when I passed security, and several men on the elevator smiling at me, I felt the panic ease a little.
The office gave me flowers and a card welcoming me back and offering to help anyway the can. I have to say that by the end of the day, I was feeling pretty happy and right now, being with you like this is a dream come true.”
It took me several days to get used to this total change. At first, I felt out of place at my desk, and my mind tried to comprehend everything that had changed. But sitting there in a dress, pantyhose, and heels had constantly distracted me from my work. Seeing my long nails attempting to use the keyboard, or taking my purse to the ladies’ room, fixing my makeup and hair, and the scent of my sweet perfume, kept me in a constant state of awe.
After a few days, things normalized as my workload increased, and there were deadlines to meet. The intense work load that piled up from my first few days back, and now took the focus off my situation. My energy went back to the piles of overdue work on my desk. By the end of the first week, I had caught up and felt comfortable at my desk. I smiled, and sat with my legs crossed as my dress displayed my long legs, now encased in pantyhose along with the sight of my high heels. I was smiling more often, and enjoying my work as a fashionable young lady.
The next few weeks were similar, and I became comfortable working and acting in my Amanda mode. Even my voice was now natural and feminine. Whenever I met a new person at the office, they introduced me as Amanda and there was never a question about my appearance. I was now living as a female, and was accepted by my staff and friends.
At the end of that first night, Lisa and Amanda shared their love again and slept in each other’s arms. Lisa loved her husband so much, and just wanted him to be happy, and deep down, she knew that this was something he had always wanted to experience. It didn’t matter to her because she didn’t marry him for his body, or having a big dick. She’s always loved him deeply and knew they would always be together.
There were promises of fun things to come and some interesting changes in their future, which would bring more love, happiness, and some interesting changes.
End of Part 2
